Rebshidduch – I got that. My point was that I’m agreeing with you that it’s a good idea.
Maybe you can try Rosie & Sherry. I think they have a dating column on Aish.com. They may have their own website as well. They may be able to answer your questions as well as refer you to a mentor.
They are “dating experts” who help people who are dating and they also train mentors. My one hesitation is that I’m not sure which segment of the population they have expertise in. I don’t know if it’s all segments or specifically older singles, or people from a certain type of haskafa/background.
But either way, I think they have mentors who are skilled at dealing with different types, so you can tell them about yourself, and hopefully, they can find the right type of mentor for you.